Tetramethylethylene

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Tetramethylethylene
Me4C2.svg
Tetramethylethylene-3D-balls.png
Names
Preferred IUPAC name
2,3-Dimethylbut-2-ene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.422 Edit this at Wikidata
EC Number
  • 209-263-8
UNII
  • InChI=1S/C6H12/c1-5(2)6(3)4/h1-4H3
    Key: WGLLSSPDPJPLOR-UHFFFAOYSA-N
  • CC(=C(C)C)C
Properties
C6H12
Molar mass 84.162 g·mol−1
Appearance colorless liquid
Density 0.7075 g/cm3 (20 °C)
Melting point −74.6 °C (−102.3 °F; 198.6 K)
Boiling point 73.3 °C (163.9 °F; 346.4 K)
Critical point (T, P) 521.0(9) K, 3.4(1) MPa[1]
insoluble
Solubility soluble in ethanol, ether, acetone, chloroform[1]
−65.9·10−6 cm3·mol−1[1]
1.4122 (20 °C)[1]
Thermochemistry[1]
174.7 J·mol−1·K−1
270.2 J·mol−1·K−1
−101.4 kJ·mol−1 (liquid)
−68.1 kJ·mol−1 (gas)
Enthalpy of fusion fHfus)
6.45 kJ·mol−1 (at melting point)
32.51 kJ·mol−1 (25 °C)
29.64 kJ·mol−1 (at boiling point)
Hazards
GHS labelling:
GHS02: FlammableGHS08: Health hazard
Danger
H225, H304
P210, P233, P240, P241, P242, P243, P280, P301+P310, P303+P361+P353, P331, P370+P378, P403+P235, P405, P501
Flash point −8 °C
401 °C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetramethylethylene is a hydrocarbon with the formula Me2C=CMe2 (Me = methyl). A colorless liquid, it is the simplest tetrasubstituted alkene.

Synthesis and reactions[edit]

It is prepared by base-catalyzed isomerization of 2,3-dimethyl-1-butene.[2]

Tetramethylethylene forms metal-alkene complexes with low-valent metals and reacts with diborane to give the monoalkyborane known as thexylborane.[3][4]

References[edit]

  1. ^ a b c d e f CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: others (link)
  2. ^ Hattori, Hideshi (2001). "Solid base catalysts: Generation of basic sites and application to organic synthesis". Applied Catalysis A: General. 222 (1–2): 247–259. doi:10.1016/S0926-860X(01)00839-0.
  3. ^ Negishi, Ei-Ichi; Brown, Herbert C. (1974). "Thexylborane-A Highly Versatile Reagent for Organic Synthesis via Hydroboration". Synthesis. 1974 (2): 77–89. doi:10.1055/s-1974-23248.
  4. ^ Giordano, G.; Crabtree, R. H. (1990). "Di-μ-Chloro-Bis(η4 -1,5-Cyclooctadiene)-Dirhodium(I)". Inorganic Syntheses. Vol. 28. Event occurs at Di-μ-Chloro-Bis(η4-1,5-Cyclooctadiene)-Dirhodium(I). pp. 88–90. doi:10.1002/9780470132593.ch22. ISBN 9780470132593.